The Art of Streetwear: How the Legends League Turned a Creative Outlet into a Brand

Since the very beginning, it’s served as a physical extension of Bryan’s creativity; a way for him to share his thoughts and feelings through streetwear.

I sat down with Bryan recently after paying a visit to his retail storefront in Toronto, affectionately called The Legends League Sweatshop. Bryan’s newest venture sits on a quiet side street off of Spadina Avenue just South of Queen West. A low-key hideout for a brand that’s been making a lot of noise.

Not only has The Legends League become a staple in the wardrobes of trendsetters and artists across the city, it’s also received cosigns from hometown heroes like Drake and Majid Jordan.

While Bryan’s recent success is impressive, if you don’t know the real story behind the brand, you’re only getting a piece of the picture.

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Finding an Audience

The initial idea behind The Legends League began in 2004 when, after a string of arrests, Bryan was placed on house arrest and filled with anger and frustration.

In an effort to put what he was feeling out into the world, Bryan turned to MySpace.

“I needed an outlet. I started writing a whole bunch of my past stories down on MySpace—like what was I going to do, yell it from a building? I was just using it as a creative outlet and a bunch of people gravitated towards the things that I was saying because, back then, not a lot of people were really being transparent online.”

Back then, not a lot of people were really being transparent online.

As his audience grew over the years, words turned to illustrations and illustrations became the foundation for something bigger. Slowly, The Legends League began to take shape on Bryan’s MySpace page.

“The whole premise behind The Legends League was essentially that everyone’s experiences shape the character that you become. Those are your legends. Everything that influences and inspires you both positively and negatively will make you the person that you are today. It sounds tacky, but that was the thinking.

My collection of my legends is my Legends League and your collection of your legends is your Legends League. Everyone’s Legends League looks different, but we can all understand the sentiment of being inspired and influenced by positive and negative experiences.”

The First Sale

By 2007, Bryan was starting to look for other ways to channel his creativity. T-shirts came as a natural next step. While he didn’t have the resources to start printing his own shirts, he did have something else: Photoshop and a built-in audience.

Instead of going the traditional route and sinking time and money into screen-printing a batch of tees, Bryan took a scrappy approach to validating his idea.

He sketched out an illustration of three recently deceased heroes—James Brown, J Dilla, and Rick James—then photoshopped his design onto a t-shirt and threw it onto his MySpace profile.

“I did these pre-orders and ended up selling like forty overnight. It wasn’t a lot in hindsight, but it felt like a whole lot. That’s basically where it all started, with this one shirt, but the community was already there.”

A Lifelong Dream

While that first t-shirt may have been the birth of The Legends League as a brand, Bryan’s love of streetwear took root much earlier in his life. In fact, from a young age, Bryan knew two things for sure: He wanted to write and he wanted to make clothes.

Like most Toronto kids in the 90s, Bryan grew up watching RapCity, an iconic MuchMusic show and open window into the world of hip hop. During one particular episode, Bryan saw Daymon Green, the owner of Toronto and NYC-based boutique Community 54, talking streetwear and promoting his former store D-Day.

Bryan, at the time only twelve years old, was instantly struck with a single thought: “I’m going to work for that guy.”

I'm going to work for that guy.

Although he was still in the sixth grade, Bryan was dead-set on showing Daymon his work and diving into the fashion world head first. He grabbed some of his designs, stuffed them into a duotang, and headed down to D-Day to talk to Daymon.

When he got to the store, Bryan was overwhelmed with nerves and backed out.

“I didn’t show him anything, but when I think about it now—as a shop owner myself—if a twelve year old came up to me like that, I’d be like: You are working for me. I’m going to make work for you.”

Bryan’s nerves got the best of him that day, but the experience also planted something deep within him—a drive to keep creating, keep designing, and start his own brand.

A Brief History of Streetwear

The foundational elements of streetwear were heavily based on what was available to the industry’s pioneers.

In its early days, there were no designer labels or fashion houses pushing streetwear lines. Instead, there were young people with passion and vision. T-shirts and hats were the materials available to them, so t-shirts and hats became the radio towers that pushed their voices out into the world.

“I feel like what’s happened now is that people associate streetwear with the clothes worn by the bulk of people who listen to a particular genre or go to certain types of bars or events. To me, streetwear is still the clothing made by the makers.”

To me, streetwear is still the clothing made by the makers.

Flash sales and pop-up shops have always been at the heart of streetwear. For most apparel startups, dropping cash into large orders of product isn’t feasible or even possible.

Instead, many streetwear brands opt to release exclusive one-and-done runs of certain pieces, harkening back to the early days of the movement when the means of mass production simply weren’t accessible to its founders.

“We used to do pop-ups. We would just pack the back of a U-Haul truck with product, park it in an alley, and I’d post a map on my Instagram. We got people camped out with food and coolers and music and tents and everything. That day, we would smash. It was one day and we’d be like: We killed it.”

Growing the Right Way

Over time, The Legends League has grown from its pop-up beginnings to a brick-and-mortar store. However, as any business owner will tell you, success always brings with it a fresh set of challenges.

As The Legends League continues to expand, Bryan now strives to balance the integrity of his brand with the savvy, strategy, and careful consideration required to run a business.

“Now I definitely see it as a business, but it’s still first and foremost an outlet for me to get these things off my chest. But you still can’t deny, especially now that we have a brick-and-mortar, the fact that you need to pay bills.”

The further Bryan pushes The Legends League forward, the more he relies on it to support his family, friends, and teammates. But Bryan remains confident that the surest path to success is by following his vision and only letting his choice of medium be affected by outside forces.

“I still think that designers that understand communicative design will always try to communicate ideas that people can relate to—whether or not you wear it on a shirt or a hat or whatever.

That, to me, has been my most effective way to communicate. I’m always going to do it. It’s just whether the application is on tees, or if it’s on pins, or if it’s on posters. That’s the only thing that’s going to change.”

Despite his growing customer base, Bryan is still dedicated to maintaining the same attitude that won over The Legends League’s audience early on. With its own storefront and quick production cycles, The Legends League is now more free than ever to stay true to streetwear’s founding principles.

“What we have now that we opened the shop and eliminated all of our wholesale accounts is the freedom to make whatever we want whenever we want. I still have that punk rock approach to it. If I feel like I want to release something, I’ll do it tomorrow. It still feels very independent to us.”

I still have that punk rock approach to it. If I feel like I want to release something, I'll do it tomorrow.

Streetwear as a Disruptive Force

It’s that independent spirit—that intense dedication to DIY principles—that makes streetwear the punk rock of the fashion world. A stripped down movement built to disrupt systems and give a voice to those who fall outside of society’s power structure.

“My son is seventeen and, in school, there are still cool kids and kids who are less accepted. That’s always going to be the case. The ones who are less accepted, if they are searching for acceptance, are going to try to go for the path that seems to be successful. It’s easy to just holler out what everyone else is hollering out or design what everyone else is designing because there’s fear in having your own opinion.

But I think most adults know that the kids who challenge stuff when they’re in school and don’t try to be like everyone else, typically do the best.”

The advantage of being different, of having a unique value proposition in a sea of options, is a sentiment that applies to streetwear, but can also be carried over to almost any industry and artform.

Just look at Kendrick Lamar: An unpredictable rapper brimming with so much creative energy that he defies imitation. If 10 years ago, you had proposed that one of the world’s top hip hop artists in 2016 would be spitting politically-charged beat poetry over jazz instrumentals, no one would have believed you.

But the exact qualities that make Kendrick so unfathomable are the same qualities that make him so successful. To Bryan, Kendrick is a perfect example of why a brand should never be playing catch up. Instead, a successful brand should be the one that you can’t catch.

“If I’m worried about the guy next to me, I’m not thinking advanced enough. I think I constantly have to remind myself that it isn’t really a competition between me and anyone else. It’s just what I’m doing.”

Know Yourself

The Legends League is the culmination of a lifelong passion for creating.

“I think a lot of people who start their own brands, if there was no one paying attention, they wouldn’t be doing it at all. For me, I was like eight when I made my first shirt. And I threw it out because I felt like if I were to show it to somebody, they wouldn’t think it was as good as the older guys that I had seen making their own shirts. Actually, I didn’t throw it out—I stuffed it in the back of my drawer because I was like: If i throw it in the garbage, maybe somebody’s going to see it and I’m going to be embarrassed.

I would be doing this whether there was the Internet or whether we had a shop or not. People who actually know that they have an opinion or are creative in a particular way, they would be doing it regardless.”﻿

People who actually know that they have an opinion or are creative in a particular way, they would be doing it regardless.

Not only is that the truth that sits at the core of Bryan’s art, it’s also the reality for makers and creatives everywhere. Entrepreneurship is about more than just starting a business: It’s about taking something within you and putting it out in the world. It’s an extension of the self; it’s creativity pulled into form.

As I wrapped up with Bryan, he left me with this story:

I have a homegirl who loves singing. She sits with me and is like, “Man, I don’t know. I just don’t feel right about my life because I’m not singing right now.”

I’m like, “What, do you have strep throat or something? You still have your voice. Are you telling me that when you go home, you don’t sing?”

She’s just like, “I don’t have the time.”

I’m like, “Man, if I could sing, every time I sighed, I’d be singing a song.”

I’ll give this advice to anybody. You already know who you are inside. Just respond to that. All you need to do is respond to that. Stop trying to do what everyone else is telling you that you’re supposed to do. Just respond to who you are inside.

You’re going to lose a bunch of friends and you’re going to lose a bunch of people who are acting like they’re you’re friends, but you’re going to shed the fat quicker and you’re going to be happier a lot sooner. When you know, creatively, that you’re supposed to be doing something, you should just be doing it regardless of the money or any of that.

At the end of the day, I am still doing this because I love it.

About the Author

Kevin Donnelly is a content creator at Shopify with an unhealthy Drake obsession.